Unhinged, A Dating Series: It’s Not That Complicated
After a memorable first date, columnist Nicolle Monico shares her thoughts on why simple gestures and thoughtfulness can score you that coveted second date
“I got my daughter from a pair of red shoes,” said the woman at the Rady Shell wrapping the VIP bracelets around our wrists. She looked down at my date’s red Nike’s and continued the story. “I was on my front lawn when a pair of shoes rolled by in the air.”
At the time, the young man had been doing a handstand on his skateboard past her privacy hedge. She could only see his red shoes as he passed by. “The rest is history,” she laughed.
My date looked at me, and smirked, “This is a good sign.”
I met Caleb (not his real name) through this column. He slid into my DMs after the first post went live, thanking me for understanding what it’s like out there. I hadn’t thought much of it at the time. I had plenty of those types of messages, along with 500 new followers in one day. When I started reaching out to a handful of locals who had messaged me to do some research and interviews, I remembered to go back to his profile.
He was intriguing, listed a bunch of hobbies on his Instagram which was filled with photos of travels. Noticeably absent, however, were pictures of his face. After reaching out for a chat, we scheduled a call a week later to talk about his dating history and the challenges he was facing as a man in his late 30s. For me, this was purely research for my burgeoning column, or so I thought.
There was an ease to our conversation on the phone. Caleb was open and honest, it didn’t feel like he was putting on a show. Still, though, I could hear some inconsistencies in what he was saying and wrote him off as someone who wasn’t ready to date.
Weeks later, I got a text from him asking me out. “Hey would you wanna get a drink sometime?” he wrote. Short and to the point, there had been no messages leading up to this. But Khruangbin, a band whose name I still can’t pronounce, was playing at the Shell and he wanted to take me. I was in.
A week later, we stood on the grass with VIP bracelets (he wanted me to be able to see, he said) discussing his red shoes. He was cuter than I expected. We talked like old friends, plenty of banter and no uncomfortable moments of silence. With a bottle of red and two wine glasses, we spent the evening chatting, laughing, and flirting.
He was child-like, overly excited to be spending time with me, giddy even. “Your eyes are like a garden,” he said at one point, calling out their hazel coloring. It wasn’t meant to be romantic, I don’t think, he was more blurting out the first thoughts that came to his mind as I took off my sunglasses. But I liked it.
I’m used to fighting for someone’s affection, so feeling wanted is new for me. And Caleb had done his homework, recalling past articles as he asked questions about me. He had clicked on each Unhinged article to learn everything he could.
Before the headliner, we got another bottle of wine. “The second one has to be more expensive, right? To show your date you’re interested?” he said. Noted. By the end of the evening, I wanted to kiss him. If you’ve been reading this column since the start, you’ll know this isn’t typical for me on first dates.
A good sign.
As my Uber approached at the end of the night, he asked if he could kiss me. It was simple, sweet. “Send me a text when you get home,” he said as he closed the car door. He asked me out the next morning and we made actual plans. We’ve talked every day since.
If I’m being honest, I didn’t want to write this post. This is a world of false starts and normally, those conversations exist only between friends and over text. If this goes nowhere, thousands of readers will know. It’ll be embarrassing. But I didn’t start this column to paint an unrealistic picture of dating. There will be lessons learned through Caleb, whether he remains in my life for a week, a season, or more.
Here’s the thing, at the end of the day it’s maybe not that complicated to show someone you’re interested in them. I think Caleb could teach a masterclass on catching a woman’s attention. He made a thoughtful first move. He took me on a cool first date, wasn’t afraid to flirt up a storm, yet remained respectful and didn’t push. He asks questions. He shows actual interest, and doesn’t (yet, at least) leave me guessing if I matter to him. Hell, he even reads my work. So for what it’s worth, hope you’re taking notes, gents.
Oh, and if you’re wondering, he no longer reads the column. “I want you to keep being completely honest with it, that’s what makes it so good…,” he texted. “If you know that I’ll eventually read it, you may alter it in some way that you wouldn’t have previously and I don’t want to do that to you and it.”
For those of you in relationships, I’m curious, what did you do to make your partner fall for you? How did you impress? Did you spring for the expensive bottle, write a love song, or do a handstand on your skateboard? Email us at @[email protected] with your story and a chance to be featured in the Unhinged newsletter.
Nicolle Monico is an award-winning writer and the director of creative projects, digital editor for San Diego Magazine with more than 16 years of experience in media including Outside Run, JustLuxe and The San Francisco Chronicle.
One year ago, I ended a relationship that I thought would be my forever. It’s strange to think in those terms, the idea of forever and all that might have happened between us, and all that will never happen now. But to see how much can change and be accomplished in only 365 days, I’m re-writing my concepts of time. I’m imbuing my future with a new kind of depth and richness I never thought possible, and I’m looking forward to what comes next.
I am writing this over the sparkling pool at my new girlfriend’s apartment. It’s a cool 80 degrees in mid-October. I’m in my bathing suit, grateful to be soaking up the last few drops of San Diego’s wildly extended summer. The person I was last year at this time no longer exists. The ideas I had for my future back then are no longer relevant. In that girl’s place is a person that I am still learning, but who I respect and admire. She’s worked hard, learned how to pick herself up, faced difficult truths, she’s been brave. And so, it’s time to once again embrace change, and bring this column to an end.
Unhinged has been the perfect sandbox to play in, in a time when I needed a safe space, a place to put my thoughts, to connect with people going through their own struggles with love in San Diego. I’m unbelievably grateful to Nicolle for passing the baton, and giving me the opportunity to share my journey, my mistakes, and my musings with you. Dating is messy, vulnerable and exhilarating. It asks you to navigate your own heart and to be deeply curious about other people.
Getting out into the scene again in my mid 30s was terrifying. I had never used dating apps, and I didn’t know how to present myself in this late-stage era of their adoption. Would I be marketable among all of these savvy users? Would I come off as some post-divorce, mid-millennial luddite? At the end of these past eight months, I’ve discovered some truths about dating and wanted to share them below.
Dating in Your 30s is Fun
I found people to be far more compassionate than I expected, and that dating in my 30s is actually a lot more satisfying than dating in my 20s. People are showing up with fascinating stories and lived experiences. They’ve made mistakes and learned from them, and have room for my story and my past mistakes, too. What matters is showing up clear-eyed about the future. I also feel more resilient about dates not working out, or needing constant communication with dates that do. My confidence in myself is bolstering my bravery to put myself out there and risk being bruised.
Not All Things That Shine Are Bright
I learned how to recognize and call out some of my old patterns, moving past the “shiny” people that at first might have seemed exciting, and challenging myself to look instead for signs of maturity and intentionality from would-be matches. The old me would have been drawn to people who have some flashy story or passion, but as I’ve gotten clear on my patterns, I know that those people make me feel competitive, and are often masking deeper insecurities. Now I’m looking for people who satisfy my core needs and don’t put me on edge.
Red Flag Meters Sometimes Need Re-Tuning
I explored vetting my red flag meter against new circumstances, asking myself to understand the core of my discomfort versus just the person’s behavior on the surface. For instance, I find myself wrestling with my aversion to sports fans. Is it the sports that are the problem? Or am I just not attracted to reckless spending on merch, games and beer? Trusting your gut instincts, reflecting on your dating history, and communicating clearly with your partner about your boundaries can head off troubles before they begin.
Today’s Dater Can Benefit From Centuries-Old Traditions
First date tension? Swiping burnout? Perhaps seeking advice from a seasoned matchmaker could be the next step in finding lasting love. I talked to Sophy Singer of Sophy Love matchmaking about the benefits of seeing a matchmaker who looks at you and your relationship goals from a holistic standpoint, identifying patterns that are stopping you from finding a fulfilling, well-matched relationship. A matchmaker can help you focus on what it is you really want, show up authentically to first dates, and encourage you to move past surface level dealbreakers or checklists like height or education level.
I’ve found that sometimes getting out of my own head, and asking other people for advice can be the key to moving forward past my own stumbling blocks or an issue I’m having in my love life. I’ve allowed myself to become very vulnerable with friends that I trust and whose relationships I respect. I’ve been surprised with the ways they have shown up, thinking about my situation with honesty and focus as I’ve moved through heartbreak to rebuilding to new relationships. It’s helped center my friends in my life in a way I’ve never done before, and now I feel that I have an extended family who loves and supports me as I am.
Despite Its Stereotype, San Diego Can Be a Great Place to Date
The great news is that San Diego is an incredible place to date. The city is thriving with people from all over the world, with endless opportunities to find love. We’ve got a fascinating cultural scene, bars and restaurants galore, hiking trails, beaches, parks. Even dating on a budget is easy, so you never have to cross your own boundaries (even financially) to see if that new person could be your person.
And if you’re sick of the apps, exploring the city alone could be your next opportunity to meet the love of your life.
There is Hope After Heartbreak
Although I have met someone new, I have no idea what the future holds. All I know is that I’m hopeful, and for perhaps the first time in my life, less afraid of the unknown. I now know what I’m capable of, and that if you lead with an open heart, the world can open to you. I also know that I’ve met someone who motivates me to be my best self. She leads by example. She inspires me every day, and I’m excited to see what we can build side by side.
We are all a perpetual work in progress. You or I will never be perfect, and we will never find the perfect match. But love is more interesting than perfection. I’m open to the journey; thanks for walking a small leg of it with me.
Earlier last month, New York real estate maven Laurie Cooper made a call to singles everywhere: “Go sit at the bar this September to meet someone.” Posting on TikTok, the octogenarian influencer urged people people to “get off the apps” and into real life, recommending a roster of New York classics—The Carlyle, The Chelsea Hotel, The Gilded Age—that could serve as the perfect backdrop for a meet-cute.
It’s no secret that today’s daters are firmly fatigued with online apps and looking for screenless alternatives to meet up with other singles. How fitting, then, that an 86-year-old real estate broker should play shepherd to greener pastures. Everywhere, from The New York Times to Bon Appetit and The Washington Post, has declared “Sit at the Bar September” a movement, this year’s newest (oldest) dating trend. So why not keep it going in October in San Diego—one of the best, most crush-worthy months in the city?
While it might at first feel uncomfortably vulnerable to leave emotional-support friends, books, and screens behind, there’s nothing sexier than owning your solidarity and inviting friendly barkeeps and perhaps a lucky fellow single to join you in a drink. So, get into your main-character energy, be brave, and check out some of San Diego’s best watering holes to kick off your “Sit at the Bar October.”
Courtesy of The Waterfront Bar & Grill
The Classic: The Waterfront Bar & Grill
Tucked away somewhat unassumingly on Kettner Boulevard in Little Italy is one of San Diego’s oldest and still liveliest drinking establishments. Opened in 1933, The Waterfront Bar & Grill possesses San Diego’s longest-held full liquor license and is one of the city’s most packed bars (most times of the day). So, it’s a great place to try being on your own for the first time, because you’re always likely to meet at least one person. Plus, you’ll be in great hands with the incredibly friendly bartenders slinging stiff and affordable drinks. Grab a burger at the bar or get a basket of complimentary popcorn and see where the night takes you.
Who You’ll Meet
During the day, you’ll find the Little Italy local who’s been coming for years. They’ll introduce you to the bartender and tell you all the insider lore. At night, say hi to the young professional, ready to dump their high-stress job at the door and show you how to party Waterfront-style. Long Island iced tea, anyone?
Courtesy of the Gaslamp Quarter
The OG: Tivoli Bar and Grill
Tivoli opened in 1885 as a saloon and still features its original wooden bar inside. Known for being one of the city’s oldest watering holes, this Gaslamp Quarter dive bar is a favorite among locals, especially during baseball season. Head here before a Padres game and channel your inner Wyatt Earp. Order a whisky to give you some liquid courage and be ready to meet your soulmate—at the very least, you’ll come away with a history lesson and a story to tell.
Who You’ll Meet
The Padres die-hard who knows it’s much smarter to order $6 whiskey sodas for pregaming than it is to shell out for the $18 beer at Petco Park.
Courtesy of Aero Club Bar
The Dive: Aero Club Bar
This much-beloved neighborhood spot off the 5 in Spruce Canyon supports a roster of regulars. It has all the trappings of a satisfying dive bar with strong drinks, friendly staff, flight-themed décor on every surface, and colorful Christmas lights strewn across the ceiling. (Because who doesn’t love a good holiday romance on a random Tuesday in October?) Aero Club is known for its whiskey collection, so consider having the bartender recommend one you’ve never tried and use it as a way to start a convo with the person next to you. Or, busy yourself with a round of pinball (the bar boasts a room dedicated to arcade games) while you work up your courage to approach the cutie playing Big Buck Hunter.
Who You’ll Meet
The tatted former hipster who’s buddies with all of the industry folks and can give you the rundown on their favorite ryes.
Photo Credit: Robert Benson
The Tiki: False Idol
Treat yourself to this speakeasy just south of Little Italy and rub elbows with true fans of tiki. Make sure to go on a weekday night when it’s less crowded but still lively enough to give you the opportunity to chat up a stranger. The bold décor and inventive drinks draw a diverse crowd, including bigtime tiki enthusiasts. And take it from us, the local scene in San Diego is full of interesting characters who you’ll want to spend your time speaking with. For drinks, rum is the name of the game. Grab a Painkiller and offer your barmate your best dad joke about its name—it’s sure to at least get a convo going.
Who You’ll Meet
They’re in full regalia for Tiki Oasis every year and might let you sample their homemade falernum if the night goes well. You can dance to Les Baxter in their palapa.
Courtesy of Happy Medium
The Hot Spot: Happy Medium
This charming corner spot in North Park opened in 2024 and offers fresh takes on cocktail classics, delicious bar bites, and a youthful vibe. Though it’s popular, there’s usually a seat at the bar. Like any good neighborhood haunt, this place is often filled with locals talking about their latest vinyl purchase or which taco shop serves the best adobada tacos. Order a Super Grass (lemongrass mezcal, tequila, lime, mango, and pandan), then get cozy and people-watch from the bar. Pro tip: Talk music to the person sitting next to you; there’s usually someone nearby who will be excited to share their album recs.
Who You’ll Meet
They’re a bookseller at Verbatim Books by day and the DJ at Soda Bar by night. They’re sweet, passionate, and impossibly cool.
Courtesy of Nine-Ten Restaurant and Bar
The Hotel: Nine-Ten Restaurant and Bar
The beauty of a hotel is that you’re sure to never run into the same crowd twice. Fresh faces and new opportunities are in high supply, and if you want the heady combination of new romance and a great drink, head to Nine-Ten, tucked inside the Grand Colonial Hotel in La Jolla. Striking the right balance of upscale yet laid-back, Nine-Ten draws an elegant and professional set looking for great food and a refined ambiance. You’ll find someone here to match your ambition and discerning standards. Start at the bar, and then head outside to the patio for a more private conversation.
Who You’ll Meet
The jet-setting sophisticate. They know their way around a wine list and might have a house in Monaco. You can impress them by ordering the pork belly.
Courtesy Visit Encinitas
The Brewery: Modern Times Beer
Looking to meet a surfy, down-to-earth cutie with great taste in hazy IPAs? Modern Times in Encinitas is the spot. Delicious brews and craveable vegan food draw in a host of outdoorsy, active North County types. The generous semi-circle bar means plenty of space to find a spot, and the chilled-out ’70s vibe makes chatting up your neighbor feel breezy. Plus, dogs are welcome, so bring your fluffy buddy for emotional support. It’s easily accessible right off the 101, so head over after your next wave sesh and see if someone catches your fancy.
Who You’ll Meet
The dawn patrol devout, who just got off work at Sun Bum next door. Their rescue dog is well-behaved, and they’re planning a trip to Hawaii next month. They’ll flirt with you over a Dungeon Map IPA and ask you for a walk on the beach afterwards.
The world’s matchmakers have been atwitter lately, according to Sophy Singer, San Diego founder and executive coach behind matchmaking service Sophy Love.
In June, Materialists hit theaters, starring Dakota Johnson as Lucy, a matchmaker for fictional New York company Adore. The film navigates not only the complicated and sometimes unrealistic expectations of her clientele but the matchmaking mathematics of Lucy’s own love life, as well.
Singer, like many matchmakers in her community, waited in anticipation to see whether the movie’s portrayal of the industry would reflect their real-life experiences. I spoke with Singer about her thoughts on Materialists.
“It didn’t portray matchmaking in a wonderful light,” she admits. “But it does remove the stigma and normalizes matchmaking [to a broader audience].”
According to Materialists, matchmaking is like working at a morgue or an insurance company: Each person is reduced to a set of rote information and statistical analyses, with a price tag to match. Men are valued primarily for their height and bank accounts, women for their youthfulness and level of education.
The film’s director, Celine Song, worked at a large matchmaking company for six months early in her career to support her aspirations as a playwright. Her experience informed much of the film’s premise, including the structure of marketability upon which Lucy evaluates each of her clients. It makes modern dating feel like the stock market—a person’s valuation rises and falls according to perceived worth.
Singer laments the “check-box driven, transactional, and slightly impersonal matchmaking process” that’s portrayed in the movie.
“What it really misses is an integrative and holistic approach. It misses the deeper, more human side of matchmaking,” she says. “For my business, it’s not just the matchmaking and the matches, but understanding our clients on a deeper level and understanding what’s holding them back.”
Singer looks at her clients not as a static set of stats, she adds, but as people capable of growth and development, with the opportunity to change their lives for the better.
“What are their patterns?” Singer wonders about her clients. “They are the common denominator, in a good way. If [people] are able to look at the underlying parts and patterns of themselves that are showing up in the dating space, that’s where the work is.”
If someone is consistently unable to make it past the six-month mark in their relationships, for example, it’s probably not because they’re too short or too old. Maybe they’re meeting quality people, but their own past traumas—either with family or early romantic partners—are prompting them to put up walls and sabotage the chance for a deeper connection. It’s a lot more complicated than the 1s and 0s approach Lucy seems to take.
In Materialists, matchmakers like Lucy throw clients into the fray without really helping them unpack what’s going on internally. In fact, if Lucy had done some more digging on one of her client’s matches, she could have potentially avoided some devastating consequences—but I won’t spoil the movie for you here.
Singer’s business uses a psychology-driven and trauma-informed modality called IFS (internal family systems) to help clients tap into what’s holding them back in the dating space. She looks at dating and relationships as the next chapter of a person’s healing and growth overall, not just the avenue to lock down a spouse and somehow live perpetually in “happily ever after.”
“There’s a huge opportunity for a completely different result than [clients have] ever had before,” she says.
Sophy argues that, when you’re not addressing the internal self and “who’s at the wheel of the bus,” you may be doomed to repeat the same cycle you’ve been in, even after accessing a dating service. Singer addresses this head-on with her clients and offers IFS-based courses for clients to learn more about themselves and identify issues they’d like to work on before meeting would-be partners.
Think of it like “match-coaching” before the more traditional matchmaking begins.
Matchmaker and founder of Sophy Love, Sophy Singer
Singer points to a particular scene in the movie: One of Lucy’s clients is crying on her wedding day, minutes before she’s set to walk down the aisle. The client admits that she’s not excited to marry her groom. He checks all the boxes, but her real motivation was to one-up her sister with a husband that she believes is more impressive than her sibling’s. “So, this is about value,” Lucy points out, making the case that marrying someone because they offer you a sense of external value is a valid reason to stay with them forever. Relieved, the mascara-streaked client moves ahead with the wedding.
But Singer holds a critical eye to this scene. “A relationship built on that level of an unconscious dynamic [is ultimately unsustainable],” she argues. At some point, what everyone else sees—that external value—will become less relevant than the fact that you’re with someone who doesn’t meet your deeper, less obvious needs. Once that happens, most people find that their attraction to that person fades fast, since the motivation to be with them was misplaced in the first place.
I ask Singer about the math of matchmaking portrayed in the movie, with perfection—or “unicorn status”—being the goal. Are people even attracted to perfection?
“There’s this problem of ‘the checklist,’” she says. “The era of dating apps has led to people treating dating as a shopping endeavor. It puts you into an evaluative mindset, and that’s how you’re showing up on dates. As people stay single longer and longer, they are not only evaluating [others], but they feel that they are being evaluated. So people are showing up in a performative manner, not as an authentic version of who they really are.”
Singer has found that people actually connect to the messiest parts of the human experience the most, because everyone understands it. She notices that women, especially, act overly low-maintenance or pretend to not have any needs when it comes to presenting themselves on dates.
“That’s not relatable. I’m trying to unravel all of that. People feel lonely and disconnected and keep having the same superficial conversations over and over,” Singer says. “They’re not understanding why they can’t connect. But that’s because they haven’t tapped into what it means to be relational and share what they’re experiencing in the moment.”
The problem is, when you show up as this breezy, unbothered version of yourself, you’re setting yourself up for failure. Not only are you less relatable in the moment, but you are creating a situation where you’re bound to lose face at some point. Once that happens, the other person may feel that you weren’t truthful about who you made yourself out to be.
Singer uses an empathetic, come-as-you-are approach to dating called “authentic relating.” The practice “allows you to reveal yourself [and also] set the stage for others to reveal themselves,” she says. “Dating can then be a gift to another person to feel seen and heard. And, when you do it that way, and it’s not about checking off a checklist, the outcome of the date doesn’t matter as much as the experience itself, and more connections can happen that way.”
Authentic relating allows each date to become less about evaluating for a perfect fit. When you let real connection happen, then finding love doesn’t have to feel like a job interview, even if you ultimately decide that person isn’t for you.
I ask if Singer felt the movie got anything right.
She laughs. “Lucy’s rant made me feel seen,” she says, referring to a scene in which Lucy drops the checklists for a moment and gives her dissatisfied clients a much-needed reality check.
“This is not a simulation. People are people are people are people. They come as they are,” she says.
Singer agrees with Lucy’s sentiments. “This isn’t Build-A-Bear!” she jokes. “An endless laundry list of perceived must-haves can lead you to overlook people who might actually be great matches for you, but don’t perfectly fill out all of your criteria.” (If you’d like to watch the rant without committing to a two-hour movie, search it up on TikTok.)
In my own life, I’ve found that checklists are often defenses against insecurity—a system of rigid rules to protect from pain and disappointment. They often tend to reflect our external ideas of worth, not authentic self-awareness. As Lucy says, “You are not a catch, because you are not a fish.”
I’m holding Singer’s advice as I navigate my own dating journey. As things move forward with Robin, I truly hope to bring my authentic self to the table. I’m trying to be honest with my flaws and not pretend that I’m perfect. And I’ve been pleasantly surprised to see her share her own insecurities with me. It makes me feel like I understand her better and can communicate with her in a way that makes both of us feel more seen. That, in itself, feels like a win—and gives me some real material to work with.
Stake Chophouse & Bar isn’t your average steakhouse. Blue Bridge Hospitality’s Coronado outpost is a modern interpretation of a big-city steakhouse nestled in the heart of the small coastal community. The team at Stake has reimagined the whole steakhouse experience. By prioritizing a seasonal farm-to-table sourcing philosophy, a personalized guest experience, and unique service touches, like a formal steak presentation and a bespoke knife selection process, Stake distinguishes itself in a sea of steakhouses.
Exceptional steaks, including Wagyu from Japan, Australia, and the U.S., and fresh seafood flown in daily form the core of Stake’s culinary identity. The menu features a five-course omakase-style steak experience highlighting house favorites, plus an array of cuts, and classic steakhouse staples—think a wedge salad, baked potato, or pasta carbonara—refined for a contemporary palate without losing their traditional appeal. Stake focuses on seasonal sourcing from the region’s best family farms and specialty purveyors, and incorporates intentionally unexpected touches to create something truly unique.
“I challenge our chefs and myself to take it a step further in sourcing,” says Chef Ronnie Schwandt. “It’s important to us to highlight different farms, unique one-off farms—whether it’s cattle, strawberries, a local fisherman or from anywhere in the United States, we’re always trying to find that niche.”
Beyond the menu, Stake emphasizes outstanding service, says Vinny Spatafore, Director of Hospitality Operations. Staff maintains detailed notes, allowing them to remember guests by name, recall previous orders such as a favorite martini (also memorable for the customer since it’s served in an extra tall, distinctly-shaped glass), and celebrate special occasions like birthdays and anniversaries.
“When you have those points of topic that you remember about a guest, they appreciate that,” he says. “Our servers are really good with that—we have a couple servers who have been here since the beginning and they’ll remember somebody from years ago, their name, their kids’ names, where they live. I’m really thankful to have a great front of house staff.”
Award-winning wines, rare whiskeys, special events, and a complementary black car service that provides transportation for guests throughout Coronado add to Stake’s appeal.
Schwandt stresses that Stake offers more than a meal; they aim to give patrons something unforgettable.
“It starts when you walk up the stairs and are greeted by the hostess—that sets the tone for the night. Then you’re greeted by a server, who may know you by name, and can guide you through the menu and curate as they get to know you,” says Schwandt. “Most people leave kind of blown away; they leave feeling like they just had an experience. That’s the goal, right? Whether you’re serving smash burgers or high-end steak, you want somebody to leave thinking, Wow, that was awesome.”
I wasn’t sure I’d ever feel butterflies for someone again. When my long-term relationship ended last year, I couldn’t have imagined that in several months’ time I’d be trading messages and stories, laughing over new inside jokes and finding so many points of connection with someone like Robin (not her real name).
I met Robin through Hinge one night while sipping wine with friends and talking about the kind of partner I’m looking for. When we connected, she started chatting with me immediately. It was a relief to not have to guess at her level of interest; she led with authenticity and vulnerability. With her, things seem a little brighter. I’m smiling a lot more. I feel like maybe the future will be much better than I even hoped for.
But at the same time, I’m also terrified of screwing it up. I constantly have that “other shoe” feeling, like I’ll make one wrong move and it’ll all be over.
In the early days of dating someone, when you still don’t know them that well, it’s impossible to know what they’re thinking about you or who they’ll turn out to be. I’m scared of ending up in the same type of situation I was in before: stifled, shut out, abandoning my own needs to try to fix something that was not salvageable or serving me.
I’m forcing myself to gut check, take a step back, vet Robin against the values I’ve instilled in myself since my breakup. What are my dealbreakers? Will I be able to enforce my own boundaries knowing that I’m so excited to see where this goes? It’s hard to temper excitement with guardrails, especially when you’re seeing someone through rose-colored glasses.
One benefit of leaving a long-term relationship is that you come away with absolute clarity about what you were missing while you were in that partnership. Hindsight looks clear as day, and you tell yourself, “I’m never going to put up with that again.” You walk through your single life with focused assurance you will never repeat the same mistakes.
And then inevitably, you meet someone new, and they bring a fresh set of variables, quirks, and baggage. You’re on the lookout for old ghosts: the poltergeist of chaotic living standards, the apparition of abandonment issues. But how should you contend with new information that may not look like the former foe you know so well?
It’s prompting me to get clear with what my dealbreakers actually are and which ones may no longer apply. What’s the difference between a true red flag—something that goes counter to my needs or values—and a trigger from my past that can be navigated with the right person?
For instance, I’ve often thought that I would never date someone who is a huge sports fan. What I’m realizing is that I don’t vibe well with people who are hyper-competitive, and I’m turned off by frivolous spending habits (like constantly buying merch, betting on sports, or attending expensive games super regularly). The subject matter of sports is beside the point—it’s the actions behind it that I’m focusing on. If my core values aren’t being violated, I find I’m much more willing to cheer for the home team.
Similarly, I have told myself that I wouldn’t again get involved with someone whose job took them away from home often (Robin’s does, as did my ex’s). But I’ve realized the issue was a lack of communication, planning, and reassurance—and the fact that my own world wasn’t as independent and developed as it needed to be for me to feel grounded when she wasn’t around. I’m realizing that I can sustain a situation like that much better if I feel prioritized by my partner when she is home and free to prioritize myself when she’s not, knowing she will check in and communicate with me in a way that makes me feel safe, not abandoned.
With all of this reflection, I can’t help running into a terrifying thought: What if what I bring is a dealbreaker for her? What if my imperfect life is just too much, and she heads for the hills? My new flame has a lot of rules for herself—she holds herself to an incredibly high standard in terms of personal growth, organization, and work ethic. I’m impressed… and intimidated.
I’m doing my best to rely on the work I’ve done on myself in the in-between. To not have the impulse to change myself in order to impress her, but to lead with my best self. My true self. This isn’t about trusting the other person to protect me but trusting myself to be resilient if we aren’t right for each other in the end. I’m motivated to get clarity about her dealbreakers, too. Is there anything there that is truly integral to who I am as a person, or is there a behavioral aspect here that I’m comfortable changing? I do think it’s fair to make accommodations for someone without it fundamentally changing who I am.
For example, I am more relaxed about home organization than she is. I’m not messy, but I will also leave the odd glass hanging around the sink or keep my hair products out if I’m in a rush. We have discussed our preferences, and she has shared that it’s more a tenant she holds for herself than for a partner. I don’t feel pressured to change how I am normally. At the same time, I’m inclined to do a little extra around the house if it means creating a space she feels comfortable in.
It’s early days, and we still have so much to discover. For now, I’ll be keeping these considerations in mind as I enjoy all the fun things, too.
Tell me, what are your dealbreakers? How early have you left a relationship because of one (or how late)? Have you ever had someone abandon you because you set a boundary or because you had something integral to you they couldn’t get past? I’m so curious.
They say you never forget how to ride a bike. Can you forget how to date? It’s been a few months now, and—nervously, a bit unsteadily, feet on the pedals—I’m doing it. I’m out there in the world, meeting people, and can say, “I am dating.” It’s fun, and it feels so different than it did when I was in my 20s.
While there are times when I pine for the innocence, optimism, and, frankly, time, that I used to have, I now feel much more self-aware, in control of what and who I want, and relaxed about not looking for a commitment too soon. But I’ve noticed a new pattern, and it feels somewhat at odds with a younger version of myself: I don’t really text in between dates. It makes me question whether I’ve forgotten how to flirt or if I’ve lost my sense of playful banter since coming out of a long-term, committed relationship. Or maybe I’m just more grown-up.
As I was making reservations at Convoy Music Bar for my third date with a new match, it occurred to me that we hadn’t communicated almost at all since our second date. It had gone well—there was flirtation, gentle jabbing, chemistry. She asked to see me again, and I confirmed with a friendly follow-up text afterwards.
But, during the week, I felt no impulse to ask her how her days were going, to send her animal memes, or to continue to build rapport when we weren’t in person.
It made me question if this could be my own defense system kicking in: Don’t get attached, play the field, be cool. “You’ve been burned too heavily to sustain more damage; now is not the time to act recklessly,” I’d think to myself. My breakup is a bouncer at the door, ready to kick anyone at a moment’s notice to keep me from experiencing pain again.
Texting can be confusing. It can make it hard to fully understand how the other person is thinking, and that’s a scary feeling. Especially in the early days when you’re just getting to know someone, the space between in-person dates can be a breeding ground for anxiety and doubt, ramping up hopes or inflating insecurity too soon.
You may have experienced this yourself: Maybe you were texting nonstop with a match, and then they suddenly ghosted, leaving you mourning a connection that never actually made it past the talking stage. Or perhaps you went out on a date only to find that your shared love of Seinfeld clips didn’t translate into real-life chemistry.
In my younger years, I would have waited impatiently for those texts to come through, for someone to affirm that I was worthwhile to them, even if we didn’t know each other that well yet. And I would read into every line, trying to divine out their real motivations. Now, I feel free, like I truly don’t need someone to continually validate the progress of our connection. If we both are feeling spark and intrigue, then great—let’s keep this train rolling. But if it doesn’t work out, that’s cool, too. I have other things going on, and other people to meet.
I’ve been following a similar impulse while on the apps, as well. Exchange a few messages, then ask to meet up. Let’s get together, enjoy a drink, take a walk. How are we connecting for real? There’s no room for mystery in my dating life anymore. It’s important to me to lead with my authentic self, share honestly with people where I’m at, and convey clearly my interest or even disinterest. No games, just the truth. It all feels like growth—and if you find yourself overinvesting in a single match even before the initial meetup or being driven crazy wondering what someone’s intentions are, it might be worth giving this low-contact approach a try.
For now, I like that I’ve set a precedent of communication that feels low-stakes. After only a few dates (and even fewer messages, sometimes), there are no hurt feelings about when to anticipate a text or guilt about not sending one or following up fast enough. I am finding that if people are interested, they make a point of letting you know. And if it feels like people are stringing you along, they probably are. I’ve stopped questioning my own instincts and allowed communication to literally speak for itself.
Of course, I also am wondering how this approach is affecting my date. So far, she seems content with the level of communication. I hope she feels respected and not ignored. Everyone is coming to the table with a different past and level of expectation.
Check back in with me in a few months. In the meantime, tell me—do you text people in between dates when you’re just getting to know them? Would it hurt your feelings if you weren’t getting regular texts after a successful first date? Am I shooting myself in the foot by not ramping up romantic anticipation? I’d love to know. Email me at [email protected] with your thoughts.
While glucagon-like peptide-1 (GLP-1) receptor agents have been used to treat Type 2 diabetes for more than 20 years, their recent emergence as weight-loss wonder drugs marked a new frontier in medicine. But their effectiveness has left some patients wondering what to do once they’ve reached their goal. Stopping the medication could mean regaining some, if not all, of the weight. A Scripps Clinic internal medicine physician recently conducted a small study of whether GLP-1 patients who had reached their goal weight could maintain that weight by taking their regularly prescribed injection every other week instead of weekly. Spoiler alert: 30 of 34 patients did. Read more about the study here and what that may mean as pharmaceutical companies roll out oral GLP-1s.
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